Hydrogen Peroxide → [(R)-3-[3-Methoxy-4-(4-phenyl-butoxy)-phenyl]-1-methyl-1-(3-oxo-1,5-dihydro-3lambda*5*-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)-propyl]-carbamic acid tert-butyl ester

HRID 2053462ノート

反応式

HRID 2053462 の反応式
[C:1]([NH:8][C@:9]([CH2:33]C)([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:16]([O:31][CH3:32])[CH:15]=1)[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)[P:38]1[O:44][CH2:43][C:42]2[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=2[CH2:40][O:39]1)C.N1C=NN=N1.[OH:56]O>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@:9]([CH3:33])([CH2:10][O:11][P:38]1(=[O:56])[O:39][CH2:40][C:41]2[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=2[CH2:43][O:44]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:16]([O:31][CH3:32])[CH:15]=1)([CH3:7])([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 41968792,4,3-Benzodioxaphosphepin-3-amine, N,N-diethyl-1,5-dihydro-HCID 12104771n-Boc-(r)-2-amino-2-ethyl-4-[3-methoxy-4-(4-phenyl-butoxy)-phenyl]-butan-1-olHCID 178418441HCID 178418441、化合物

生成物 1

HCID 59655585[(R)-3-[3-Methoxy-4-(4-phenyl-butoxy)-phenyl]-1-methyl-1-(3-oxo-1,5-dihydro-3lambda*5*-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)-propyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-Boc-(R)-2-Amino-2-ethyl-4-[3-methoxy-4-(4-phenyl-butoxy)-phenyl]-butan-1-ol (0.23 g; 0.5 mmol) in THF (5 ml) is added N,N-diethyl-1,5-dihydro-2,4,3-benzodioxaphosphepin-3-amine (0.24 g; 1 mmol) and tetrazole (0.11 g; 1.5 mmol). After 2 hours at RT H2O2 (30% in water; 0.58 ml) is added and the mixture is kept at RT for further two hours. The reaction mixture is quenched with Na2S2O3 and extracted with ethyl acetate and then washed with aqueous citric acid and aqueous saturated NaHCO3 solution. The organic layer is dried and concentrated and then purified on a silica gel using dichloromethane/ethanol (95/5) as mobile phase.

後処理

  1. customThe reaction mixture is quenched with Na2S2O3
  2. extractionextracted with ethyl acetate
  3. washwashed with aqueous citric acid and aqueous saturated NaHCO3 solution
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. custompurified on a silica gel

出典と根拠

ORDレコード
ord-3cfdffc33a39494aafa46533749d0f92
出典データセット
uspto-grants-2008_02
特許番号
US07326801B2

反応ノート

読み込み中…